The effect of various substituents on the reactivity of aromatic amines in some reactions has been studied. The electronegativity of the substituent and its position (e.g. ortho, meta, and para) on the amine has an effect on the reactivity of the amine in chemical reactions including electrophilic aromatic substitution reactions. One set of papers discussing this is by M. Miocque and J. M. Vierfond in the Bull. Soc. Chim. Fr. (1970), volume 5, pages 1896, 1901, and 1910.
It is known that one of the degradation products of thermal decomposition of aromatic amine containing benzoxazine polymers is the aromatic amine. It has been proposed to add acetylene, phthalonitrile and nitrile functional groups to an aromatic amine to generate an additional chemical bond between the aromatic amine and the rest of the polybenzoxazine network. Conceptually, the added chemical bond would decrease the amount of aromatic amine volatilized thereby increasing the thermal stability of the benzoxazine polymer. This was effective, but the aromatic amines with the acetylene, phthalonitrile and nitrile functional groups are difficult to prepare and significantly raise the product's cost.